2021 NBA free agency: Kyle Lowry is the All-Star addition Miami Heat waited for, but did they wait too long?

At Jimmy Butler’s Miami Heat introductory press conference in 2019, Pat Riley was already being asked about the next move. At the time, Russell Westbrook was being thrown around. Chris Paul became a name after he was dealt to the Oklahoma City Thunder and looked to be on a mere layover. A lot of names get connected to the Heat. They’re a first-class organization in a glitzy city with unwavering eyes on winning. Butler, as the prevailing sentiment went, wasn’t enough on his own to turn Miami into a contender.  

But then he did, taking them to the Finals in 2020. Along the way, the Heat have resisted the temptation to over-leverage themselves with name-value moves. No Westbrook. No Paul. At the 2020 trade deadline, when they landed Andre Iguodala from the Memphis Grizzlies, it appeared they were going to bring in Danilo Gallinari as well as part of a bigger three-team trade.  

It would’ve been the easy thing to do. Gallinari would’ve helped them immensely as a knockdown 3-point shooter and viable isolation option in the playoffs, and the heat, so to speak, was on to maximize Butler. But the Heat passed.  

It was rumored that Gallinari, who was set to become a free agent in the summer of 2020, wanted a bigger extension than Miami, which was saving its space for a run at Giannis Antetokounmpo, was ready to give out.  

Then came this past February’s trade deadline, when the Heat were heavily connected to Kyle Lowry, for whom Toronto was trying to find a championship-contending destination while also guarding against losing Lowry for nothing as an impending free agent. Again, it seemed like a big name was headed to join Butler and Bam Adebayo, but the Heat, again, held their ground.  

Word was the Raptors wanted at least one of Duncan Robinson or Tyler Herro, and Miami wouldn’t budge knowing it had a good chance to get Lowry in the summer without having to give up one of its two most prized young players.  

It worked. On Monday, the Heat reportedly came to a sign-and-trade agreement with Toronto to land Lowry, sending Goran Dragic and Precious Achiuwa back to the Raptors. No disrespect to Dragic or Achiuwa, but clearly waiting a few extra months paid off in terms of who the Heat had to part with to get Lowry. Now they still have Herro and Robinson, the latter of whom they just extended on five-year, $90 million deal, which represents the largest contract ever awarded to an undrafted player.  

So everything’s set, right? The Heat got their guy without giving up any of their guys, seemingly a cake-and-eat-it-too situation. But did they wait too long? We didn’t know it at the time, but the 2020 championship was wide open. The Heat already made the Finals, and perhaps Gallinari, or certainly Paul, or maybe even Westbrook, could’ve put them over the top against the Lakers in the bubble.  

This past season, as contending teams fell apart with a rash of injuries unlike any postseason many of us can recall, the title was yet again as open as it’s been in years. Paul got the Phoenix Suns to the Finals, and the Milwaukee Bucks, whom the Heat beat in 2020 before being swept  in the first round this season, won it all. Would moving for Lowry at the deadline at the expense of Herro or Robinson have made the difference in Miami possibly getting past Milwaukee, or ending up with a better first-round matchup via a higher seed, and potentially making another late run?  

Probably not. In that particular case, the Heat certainly did the right thing in retaining Robinson and Herro while still landing Lowry anyway. But remember when they, like almost every other team, didn’t want to commit to a long-term deal for Chris Paul? That’s a deal that would’ve, in hindsight, made them a certain contender, but with the way Paul has played in Oklahoma City and Phoenix, has it also created a deceiving comfort in paying old players a ton of money?  

The Suns and Paul just agreed to a four-year extension that could be worth up to $120 million, taking him through his age-40 season. Mike Conley got three years and $72.5 million from the Utah Jazz, taking him through his age-36 season. The Heat, meanwhile, handed Lowry a three-year, $90 million deal that will take him through his age-38 season.  

Any one of these guys could fall off a proverbial cliff any time. It’s likely to happen more gradually than that, but in the particular case of the Heat, it would seem to be imperative that they maximize the front end of that deal before Lowry potentially becomes a salary-cap-clogging, aging All-Star who can no longer factor heavily into a championship formula.  

Butler, by the way, will be 32 by the start of next season, and Miami just gave him a reported four-year, $184 million extension. This is a lot of money to some not-exactly-spring-chicken players. The Heat were patient and wound up with Lowry, but the question is: Did they wait too long. Assuming health, there are some monster teams out there for Miami to contend with that it potentially could’ve avoided these past two years had the Heat been ready to win a title earlier. 

We’ll see if Lowry is enough against a full-strength Brooklyn Nets or the defending-champion Bucks or even against a potentially reshaped Philadelphia 76ers team likely headed for a Ben Simmons trade. My guess is the Heat are still a good way short of the elite teams, but then again, I thought that in 2020 as well. 

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